(2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate

Base Information

Chemical Name:(2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate
CAS No.:1450984-45-8
Molecular Formula:C₂₂H₃₅NO₅Si
Molecular Weight:421.609
Hs Code.:

Synonyms:(2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate

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Chemical Property of (2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate

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Technology Process of (2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate

There total 8 articles about (2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 6081-61-4
N-(benzyloxycarbonyl)-D-serine

: 1450984-45-8
(2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate

Guidance literature:: Multi-step reaction with 7 steps

1: 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 1.5 h / 0 - 25 °C / Inert atmosphere

2: boron trifluoride diethyl etherate / acetone / 15 h / 25 °C / Inert atmosphere

3: diethyl ether / 2 h / -78 °C / Inert atmosphere

4: zinc tetrahydridoborate*Et₂O; cerium(III) chloride heptahydrate / methanol / 2.5 h / 0 - 25 °C / Inert atmosphere

5: water; acetic acid / 15 h / 50 °C

6: pyridine / 1 h / 0 °C / Inert atmosphere

7: pyridine / 0.67 h / 0 - 25 °C / Inert atmosphere

With 4-methyl-morpholine; pyridine; zinc tetrahydridoborate*Et₂O; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; water; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In methanol; diethyl ether; dichloromethane; acetone;
DOI:10.1039/c3md00033h

Reference yield:

: 1092473-80-7
(R)-benzyl 3-hydroxy-1-(methoxy(methyl)amino)-1-oxopropane-2-ylcarbamate

: 1450984-45-8
(2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate

Guidance literature:: Multi-step reaction with 6 steps

1: boron trifluoride diethyl etherate / acetone / 15 h / 25 °C / Inert atmosphere

2: diethyl ether / 2 h / -78 °C / Inert atmosphere

3: zinc tetrahydridoborate*Et₂O; cerium(III) chloride heptahydrate / methanol / 2.5 h / 0 - 25 °C / Inert atmosphere

4: water; acetic acid / 15 h / 50 °C

5: pyridine / 1 h / 0 °C / Inert atmosphere

6: pyridine / 0.67 h / 0 - 25 °C / Inert atmosphere

With pyridine; zinc tetrahydridoborate*Et₂O; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; water; acetic acid; In methanol; diethyl ether; acetone;
DOI:10.1039/c3md00033h

Reference yield:

: 656827-13-3
(R)-benzyl-4-(methoxy(methyl)carbamoyl)-2,2-dimethyloxazolidine-3-carboxylate

: 1450984-45-8
(2R,3S)-2-((benzoxycarbonyl)amino)-1-[(tert-butyldimethylsilyl)oxy]hex-5-en-3-yl acetate

Guidance literature:: Multi-step reaction with 5 steps

1: diethyl ether / 2 h / -78 °C / Inert atmosphere

2: zinc tetrahydridoborate*Et₂O; cerium(III) chloride heptahydrate / methanol / 2.5 h / 0 - 25 °C / Inert atmosphere

3: water; acetic acid / 15 h / 50 °C

4: pyridine / 1 h / 0 °C / Inert atmosphere

5: pyridine / 0.67 h / 0 - 25 °C / Inert atmosphere

With pyridine; zinc tetrahydridoborate*Et₂O; cerium(III) chloride heptahydrate; water; acetic acid; In methanol; diethyl ether;
DOI:10.1039/c3md00033h